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Johnny Depp And Winona Ryder
Length of Engagement: 3 years 

Johnny Depp met Winona Ryder on the set of Edward Scissorhands in 1990, and just five short months later they were engaged. But that didn't mean they rushed to the chapel. The two dated for three years until Ryder's father put a stop to the engagement, saying, "At 19, Winona is too young to marry."